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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Gael Monfils | Indian Wells Masters | 2005-03-07 | Indian Wells Masters | 2026-03-05 | 7668d (21y 3d) |
| 2 | Richard Gasquet | Miami Masters | 2003-03-17 | Shanghai Masters | 2023-10-02 | 7504d (20y 204d) |
| 3 |  Tommy Haas | Miami Masters | 1997-03-17 | Miami Masters | 2017-03-20 | 7308d (20y 8d) |
| 4 |  Stan Wawrinka | Indian Wells Masters | 2006-03-06 | Shanghai | 2025-09-24 | 7142d (19y 207d) |
| 5 |  Feliciano Lopez | Miami Masters | 2002-03-18 | Indian Wells Masters | 2021-10-04 | 7140d (19y 205d) |
| 6 | Fabrice Santoro | Miami Masters | 1990-03-16 | Miami Masters | 2009-03-25 | 6949d (19y 14d) |
| 7 | Fernando Verdasco | Miami Masters | 2003-03-17 | Miami Masters | 2022-03-21 | 6944d (19y 9d) |
| 8 |  Andy Murray | Indian Wells Masters | 2006-03-06 | Miami Masters | 2024-03-18 | 6587d (18y 17d) |
| 9 |  Marin Cilic | Indian Wells Masters | 2008-03-13 | Miami Masters | 2026-03-19 | 6580d (18y 10d) |
| 10 |  Kei Nishikori | Indian Wells Masters | 2008-03-13 | Cincinnati Masters | 2025-08-07 | 6356d (17y 151d) |